Journal of the Iranian Chemical Society最新文献

We present the synthesis of a novel series of tri-substituted methane (TRSM) derivatives via an efficient one-pot, three-component reaction. This reaction combines 4-hydroxybenzo[h]quinolin-2(1H)-one, aromatic aldehydes, and 1,3-dimethyl-6-aminouracil, catalyzed by L-proline in ethanol. Our primary aim is to create a new TRSM scaffold by incorporating diverse pharmacophore moieties into a unified structure, providing a foundation for future drug discovery and medicinal chemistry studies. Key advantages of this approach include the use of an organocatalyst, a streamlined experimental process, and the absence of toxic byproducts. Notably, the methodology eliminates the need for time-consuming column chromatography, offering a cleaner, more efficient synthesis. The chemical structures of the products were confirmed through IR, NMR, mass spectrometry, and elemental analysis, validating the successful formation of the desired derivatives.

The synthesis of a Schiff base ligand 5-(((7-chlorobenzo[d]thiazol-2-yl)imino)methyl)-2-methoxyphenol (L) derived from the condensation of 5-amino-1,3,4-thiadaizole 2- thiol and 3-hydroxy-4-methoxy benzaldehyde and its Cu(II), Co(II), Mn(II), Ni(II), and Zn(II) metal complexes in 2:1 stoichiometric ratio (2HL:M). The formation of the ligand and its metal complexes were evaluated using MS technique, FTIR, UV–visible, ¹H-NMR, ¹³C-NMR, and thermogravimetric analysis. Molecular docking studies were conducted using AutoDock 4.2 to predict the binding affinity and interaction of L and its metal complexes with potential biological targets. The larvicidal activity of L and its metal complexes was evaluated by exposing larvae to various concentrations of the compounds. The mortality rates of the larvae were determined after 24 h of exposure. The Cu(II) complex exhibited the most effective larvicidal activity, with a mortality rate of 66%. The survival rate of the larvae exposed to the Cu(II) complex was only 34%, indicating its high toxicity. The free Schiff base ligand showed moderate larvicidal activity with a mortality rate of approximately 50%, meaning roughly half of the larvae survived. This suggests that while L is somewhat effective, its larvicidal activity is significantly enhanced upon metal coordination, especially with Cu(II).

Photocatalytic water splitting has emerged as a pivotal strategy to tackle global energy crises and environmental degradation by producing clean hydrogen. In this study, a novel Cu₂O/CuO/C composite photocatalyst was prepared from cupric nitrate trihydrate and 1,3,5-benzenetricarboxylic acid via the two-step solvothermal-calcination method as the photocatalyst for hydrogen evolution. Advanced characterization techniques, including X-ray diffraction (XRD), scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS), ultraviolet–visible diffuse reflectance spectroscopy (UV–Vis DRS), transient photocurrent responses, electrochemical impedance spectroscopy (EIS), linear sweep voltammetry (LSV), and Mott-Schottky test, confirmed the composite's excellent visible and near-infrared light absorption and Z-scheme heterojunction architecture. Its remarkable performance originates from the effective p-n heterojunction formed between Cu₂O and CuO. Upon a 300 W xenon lamp (350 < λ < 780 nm) illumination, photogenerated electrons and holes are produced in Cu₂O and CuO, respectively. Electrons from the conduction band (CB) of CuO migrate to the valence band (VB) of Cu₂O, recombining with holes. This mechanism not only enhances charge separation and extends carrier lifetime but also preserves the strong reducing capability of Cu₂O, significantly boosting photocatalytic activity. The composite achieved a hydrogen production rate of 511.07 μmol/(g h). Notably, it retained stable performance over three consecutive cycles without significant activity loss, demonstrating robust durability. These findings highlight the potential of Cu₂O/CuO/C Z-scheme heterojunctions as efficient, stable photocatalysts for sustainable hydrogen evolution.

In this study, thiophene carboxamide derivatives were synthesized and structurally confirmed using NMR, FT-IR, UV–visible, and ESI–MS techniques. Their anti-inflammatory and anti-diabetic activities were assessed through in vitro assays, while molecular docking was used to evaluate interactions with key enzymes (1-HNY, 1-PGG, and 4-COX). Additionally, DFT calculations provided insights into electronic structure, molecular electrostatic potential, and reactivity patterns. The compounds showed significant inhibition in biological assays, correlating well with binding affinities and charge distribution analyses. Structure–activity relationships were supported by frontier molecular orbital analysis, highlighting the influence of electron-donating and withdrawing substituents. The integration of experimental and computational analyses highlights these derivatives as promising candidates for therapeutic development.

The aim of this work was focusing on comparison study through photo-Fenton-like catalysts. The effect of Iron III was investigated in two different cases by using layered double hydroxide of MgAl and MgAlFe in which were synthesized by co-precipitation method. In this sense, adsorption and photocatalytic degradation were examined to measure the performance of each catalysts for Congo red removal. The physic-chemical properties of MgAl and MgAlFe were characterized by X-ray diffraction (XRD) scanning electron microscope (SEM), Brunaur-Emmet-Teller (BET), Fourier transformed infrared (FTIR) spectra, thermogravimetric analysis TGA, and point of zero charge (PZC). Our results demonstrate higher adsorption and degradation at naturel pH by MgAlFe compared to the MgAl. Meanwhile, the time dependence of Congo red was well fitted by pseudo-second-order model with R² > 0.999. The most accurate isotherm was Freundlich with R² > 0.999. The operated parameters confirm that the best degradation was at acidic pH, and at natural pH respectively for MgAl and MgAlFe. In conclusion, the results obtained suggest that the heterogeneous photo-Fenton-like has excellent properties and the ability to remove Congo red in both cases adsorption and photocatalytic degradation.

Cetuximab and Tocilizumab are significant therapeutic monoclonal antibodies used in the treatment of head and neck malignancies and severe COVID-19 pneumonia, respectively. Given their potential interaction with peanut lectin, patients receiving these therapies should avoid consuming peanuts. In this study, we present a comprehensive multimodal approach using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), high-resolution mass spectrometry (Q-IMS-TOF MS), and size exclusion chromatography to investigate the interactions between these antibodies and lectin derived from peanuts. The role of glycan structures in mediating these interactions was analyzed. For Cetuximab, the glycans identified included G0F, G1FN, G2F, G0, G1, G2, G0N, G1N, M5, and M6. Among these, G1, G2, and M6 were not involved in binding with peanut lectin. In Tocilizumab, the glycans G0F, G1F1, G1FN, G0, G1, G2, G0N, G1N, M5, and M6 were detected, but only G0F, G1F1, and G0 participated in lectin interaction. This detailed glycan analysis provides valuable insights into the specific glycan-mediated binding mechanisms between monoclonal antibodies and lectins, which may inform future therapeutic strategies and dietary considerations for patients undergoing antibody treatments.

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A series of thirteen novel pyrazolyl pyrazole–thiazole hybrids (5a–5k, 6, 7) and two pyrazolyl-pyrazole hybrids (8, 9) were designed, synthesized, and structurally confirmed by ¹H-NMR, HRMS, FT-IR, ¹³C-NMR, 2D-NOESY spectroscopic techniques, and elemental analysis. The pyrazole–thiazole hybrids (5a–5k) were obtained by the Hantzsch reaction between the thiosemicarbazone 4 and 2-bromo-1-phenylethanone derivatives in ethanol at ambient temperature. The antimicrobial potency of synthesized hybrids was evaluated by inspecting them against S. aureus, E. coli, S. pyogenes, P. aeruginosa, C. albicans and A. niger pathogens. Most of the compounds (3, 5a, 5d, 5e, 5j, and 9) exhibited significant antibacterial effectiveness with a MIC value of 62.5 µg/mL as compared with positive control chloramphenicol and ciprofloxacin (MIC = 50 µg/mL). Additionally, pyrazole–thiazole hybrids 5g, 5h, and 7 proved their significant antifungal potential with an MFC value of 250 µg/mL, in contrast, compounds 5b, 5e, 5f, 5k, and 6 exhibited equal antifungal potential against C. albicans in comparison with positive control standard antifungal agent Griseofulvin (MFC=500 µg/mL). The study on molecular docking demonstrated that the compounds 5a, 5d, 5e, and 5j bind the nitrogenous bases of DNA gyrase of the targeted 2XCT protein with the binding affinity of − 9.3, − 9.6, − 9.3, and − 9.3 kcal/mol, respectively. Our synthesis, antimicrobial analysis, and molecular docking study suggested that the pyrazole–thiazole hybrids 5a, 5d, 5e, and 5j provided an important reference for further progression in the antibacterial drugs.

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To develop the layered magadiite as the carrier of anticancer drugs, the intercalation and kinetic release of methotrexate (MTX) from cetyltrimethylammonium bromide (CTAB)-modified magadiite has been studied. X-ray diffraction (XRD) result showed that the basal spacing of magadiite varied from 1.54 to 2.87 nm while the magadiite was modified with CTAB, and then the basal spacing was up to 3.55 nm after the methotrexate was intercalated into the CTAB-modified magadiite. Zeta potential test revealed that the zeta potentials changed during the modification and intercalation. Compositional analyses suggested that loading capacity of the drug delivery system based magadiite for MTX was about 11.40%. In vitro drug release suggested that the drug release either in phosphate buffer solution (PBS, pH = 7.4) or in HCl solution (pH = 1.35) exhibited ExpDec3 mode. The releasing percentage of drugs was about 59.12% or 72.3% after drug release in PBS for 120 h or in HCl solution for 700 min, respectively. Moreover, the drug release exhibited good reproducible. These results indicate that the magadiite may be a promising carrier of MTX.

An eco-friendly approach for the synthesis of Fe₂O₃ and CuO nanoparticles using onion (Allium sepa) extract was compared with pristine chemical synthesis. The confirmation of copper oxide and iron oxide nanoparticles was done by using Fourier transform infrared, Ultraviolet–Visible spectroscopy, X-ray diffraction, and scanning electron microscopy with energy-Dispersive X-ray analysis (SEM–EDX). The band gap was calculated via Wood and Tauc relation. The crystallite sizes of nanoparticles were calculated using Debye–Scherrer and Williamson–Hall equations using X-ray diffraction. SEM–EDX has confirmed the surface morphology and elemental analysis of nanoparticles. Antibacterial activity has been performed against two bacterial strains Bacillus subtilis (gram + ve), and Psuedomonas aeruginosa (Gram -ve). The photocatalytic activity of nanoparticles was observed against methylene blue in UV light. The pristine Fe₂O₃ and CuO nps reusability has been checked for MB after four successive cycles. The decrease in band gap results in an increase in the percentage degradation with relation to crystallite size and particle size of nanoparticles. The antibacterial activity of green synthesized Fe₂O₃ and CuO nanoparticles showed greater efficiency when compared to the pristine nanoparticles.

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